Stronghold in the Highlands

Foreword by Joe Proscia: As a group, Proactive recently adopted the trails leading to the North and South Redoubts, part of the Hudson Highland State Park Preserve. The trail immediately clicked with us, with views of Storm King (one of those mountains I personally feel a strong connection to), the Hudson River (a constant presence on most of our travels and in my very own neighborhood), and a fantastic view of West Point (strategically, this location was very important in the Revolutionary War history of America's most storied military academy, acting as a keep defensive position). I hope you are just as fascinated as I was with the story of West Point and the surrounding region. Take a moment to transport yourself back in time in your mind and imagine bearing witness to the historical events that took place in the hills of the Hudson Highlands. Enjoy!

Early in the fight for America's independence, it became clear that control of the Hudson River and its valley was vital to the success of both sides. It proved to be one of the most important routes for distribution of troops and supplies throughout the Northeast and New England. Most importantly, however, British seizure of the Hudson would have split the colonies in half -- separating GA, SC, NC, VA, MD, DE, PA, NJ, and NY from CT, RI, MA, VT, NH, and ME (at the time a part of Massachusetts). This would have all but ensured a British victory.

The Hudson River's surroundings are characterized by plains up and down its length. Fortifications built on the wide-open Hudson Valley would be vulnerable from several directions. Eventually, the combatants realized that control of the entire river would lie in a small section of extremely rugged terrain -- the Hudson Highlands.

The Patriots' first major attempt to secure this corridor was in the construction of a fort located on Martelaer's Rock. The island was named by the earliest Dutch explorers after a word meaning "martyr" or "struggle". This refers its location on a bend of the Hudson that proved very difficult to navigate due to river angle and north winds. It came to be known as "World's End" by English speakers. Built in 1775, the fortification was named Fort Constitution, resulting in Martelaer's Rock being renamed Constitution Island. Due to logistical difficulties in constructing the fort, it was eventually abandoned. A new, more effective location was proposed to the south near Anthony's Nose, and Fort Constitution's remaining materials were diverted to this new site. The British took Constitution Island in 1777 and destroyed the unfinished fort.

This new site became the location of Fort Montgomery. It would guard a heavy chain that stretched from the fort across the river to Anthony's Nose meant to deter, delay, or outright deny naval access to the north. Realizing the strategic importance of high ground located to the south across the Popolopen Creek, the Americans constructed Fort Clinton to reinforce Montgomery. The two forts were heavily reliant on one another, connected by a simple pontoon bridge across Popolopen.

Though impressive, their extensive designs required a great number of troops to operate the forts -- numbers which weren't available. Before Fort Clinton was officially completed, Tories and British regulars attacked both forts simultaneously from the west with support from the British Navy on the Hudson itself. The battle turned when the Popolopen Creek pontoon bridge was compromised, cutting off supply exchange between Clinton and Montgomery. The British destroyed the forts and dismantled the chain before returning to the City of New York -- injuring, capturing, or killing more than half of the Patriots stationed there.

In the time since the Battle of Fort Montgomery, the Patriots regained control of Constitution Island in 1778. To solidify their hold on the Highlands corridor, the Continental Army occupied a peninsula on the river directly across from Constitution Island named "West Point". This time, Constitution Island would not be the site of a stronghold but would instead provide support to main fortifications across the river. Under the direction of a bright Polish engineer named Tadeusz Kosciuszko, two state-of-the-art garrisons were built on West Point.

The inland fort was named Fort Putnam after Colonel Rufus Putnam, whose men where responsible for the physical construction of the garrison. It was built in support of a fort positioned directly on the river, which guarded a new chain on the Hudson. Together with an extensive array of fortifications on both sides of the river (including newly constructed works on Constitution Island), the entire system became known as Fortress West Point. The crucial riverside garrison would be named Fort Arnold after its first commander: Major General Benedict Arnold.

Benedict Arnold was an accomplished military officer, from leading campaigns in Ticonderoga, Quebec City, and Saratoga, to assuming military command of the entire city of Philadelphia. During this time, however, his association with the Continental Army began to grow cold. In his eyes he was passed over for several promotions, removed from command more than once, and denied recognition for his work -- particularly in Saratoga. Arnold also began to associate socially with high-class members of British-loyalist Tories. One particular loyalist named Peggy Shippen eventually married Arnold. She was said to exert powerful influence over her husband and would go on to become Britain's highest paid spy. These factors combined to destroy his relationship with his Patriot peers, and the damage proved irreversible.

He set forth on a mission to attain leadership of Fortress West Point, which became a success. His goal was not to strengthen the Patriots' hold on the Hudson Highlands corridor, but to deliver West Point to the British with very little to no loss on the part of the Crown. Through intermediaries, Arnold negotiated with General Henry Clinton of Britain to deliver information compromising West Point for 20,000 pounds and a command in the British army. Peggy Shippen was responsible for delivering to her husband the letter containing Clinton's acceptance of terms.

Benedict Arnold was given command of the entire system of West Point fortifications on August 3, 1780. He began his West Point campaign by weakening defenses, diverting resources, and delaying repairs to ensure the success of a potential British siege. Through his main contact, British spy chief Major John André, he would provide the opposition with troop statistics, maps of west point defenses, and detailed inventories. Arnold had written passes to allow Major André to pass through enemy lines under the alias "John Anderson". However, André was stopped by militamen on September 23rd while traveling on Albany Post Road in Tarrytown. Plans for capturing West Point were found in André's boot, leading to his arrest.

On the morning of September 25th, George Washington had intentions of meeting at Arnold's house for breakfast and a tour of Fortress West Point. He stopped on the way to the meeting to tour the North and South Redoubts. George Washington was in the process of inspecting the South Redoubt just as Arnold was learning of André's capture. When Washington arrived at Arnold's home, he had already fled across enemy lines to City of New York.

Washington had attempted to negotiate a prisoner exchange with Britian, sending André to the British in exchange for Arnold. Clinton refused. As a result, Major John André was hung in Tappan, New York and buried nearby. Washington sent spies into the City of New York to capture Arnold but the plan failed when Arnold unexpectedly changed residences before heading for the Virginia theater of war. Arnold wrote Washington a letter, requesting safe passage for his wife Peggy Shippen to the City of New York. Washington granted the request.

For his role in the plot, Arnold's commission was reduced to just over 6000 pounds, but was given a role as brigadier general in the British Army. Shortly after the surrender of General Cornwallis at Yorktown, VA, Arnold left America for England. He died in London in 1801 and by that time garnered a reputation among Britons far less honorable than Major John André.

In the time since the events of September 1780, Fort Arnold was renamed Fort Clinton after Major General James Clinton, who served under Washington in the Siege of Yorktown. Of the plaques at West Point commemorating Revolutionary War generals, the only mention of Benedict Arnold is a plaque reading "Major General, Born 1740" with no name.

Training at West Point began as early as 1794. United States Military Academy was officially established on July 4th, 1802. West Point remains the oldest continuously military outpost in the United States since Brigadier General Samuel Parsons crossed the Hudson River ice in January 1778.

A number of Fortress West Point's features still remain to this day in varying degrees of condition. Fort Putnam stands today

and is open for visits in the summer and selected fall days. The original chain battery still exists in a restored state. A section of the chain itself is on display not far to the west. Key features that have been destroyed are often marked with plaques and/or statues. Constitution Island and its fortifications are available for tour. Visitors arrive by boat from West Point's South Dock.

A major factor contributing to the security of Fortress West Point was the system of "redoubts" surrounding the vicinity. A redoubt is defined as a structure enclosed on all sides, generally made of earthworks supported by a wooden frame. To provide adequate cover, walls were at least 6 feet high. Wall heights were typically augmented by outer trenches dug at the base of the wall. Inside, banquettes or steps were built for infantry to be able to fire over the top of the wall. A redoubt's resistance to types of enemy fire were dependent on the thickness of its tapering walls measured from the top -- 2 feet would resist musket fire, 3 or more feet resists lightweight cannon fire, and a thickness of up to 7 feet would resist heavier 12-pound cannons. Resistance to the heaviest artillery would require depths up to 18 feet. The standard redoubt configuration was square; however the circumstances of the battlefield and surrounding terrain had a large effect on the pattern. This led to redoubts shaped like stars, pentagons, trapezoids, circles, and other shapes. As such, square redoubts were rare at Fortress West Point.

These small fortifications were set up in mutually-supporting positions around the area. They were intended to provide defense and cover fire for each other, Forts Putnam and Arnold, and crucial batteries. On West Point itself, four numbered redoubts protected Fort Putnam from above. Several of these redoubts still exist in reasonable condition today. Closer to the river, Forts Wyllis and Webb were essentially large redoubts set up in defense of Fort Arnold. Sherburne's Redoubt was another riverside fortification, marked only by a boulder and plaque today. In the Hudson itself, Fort Constitution had its own system of batteries and redoubts. Redoubt No. 7, on Constitution Island's southwestern edge, is in particularly good condition today.

On the east side of the river, three redoubts were planned as the outer ring of West Point's defenses. They primarily guarded land approaches, though the southernmost would potentially have a clear view of all northbound vessels as they passed Anthony's Nose. Sugarloaf Hill would hold the southernmost redoubt named "Sugar Loaf" and Fort Hill would contain two mutually-supporting redoubts named "Middle" and "North".

However, Sugar Loaf was never developed. Middle Redoubt then became the South Redoubt, which was the key fortification on Fort Hill. Requiring 160 troops to operate, it had a commanding view of West Point and Constitution Island. It also held sightlines to the Wallkill Valley north of the Butter Hill -- modern day Storm King Mountain -- but it is unclear if this was a factor in its location or intended purpose. North and South Redoubts were commissioned by George Washington in July 1779, designed by Brigadier General Louis Lebègue Duportail, and completed before the end of the year. Benedict Arnold's tactical reports provided to Major John André specifically mentioned details about the North and South Redoubts.

The installations on Fort Hill were among the first lines of defense at West Point. Together with the fortifications across the river, their presence helped deter the British from ever launching an attack on the imposing Fortress West Point. North and South Redoubts never saw combat as a result. It is the security of West Point and control of the north-south flow of troops and supplies that directly contributed to the success of the Continental Army in the Revolutionary War, culminating in the events of Yorktown, VA only a year after Benedict Arnold's betrayal. At the conclusion of the war, the North and South Redoubts were abandoned in 1783. Being constructed of earthworks rather than masonry, they have since eroded away -- leaving only traces of their existence.

Today, the locations of the North and South Redoubt are found in and near the Garrison School Forest, which was formed from land donated by the Sloan and Osborn families (Osborn is same family that owned nearby Castle Rock). The location of the South Redoubt continues to be West Point's most direct overlook from the east side of the Hudson River. It allows hikers to experience the same view George Washington saw just moments before meeting with Benedict Arnold -- a meeting that never happened.

Fort Hill is served by the North Redoubt Trail, developed and maintained by members of the New York-New Jersey Trail Conference with assistance from the Hudson Highlands Trail Crew and Proactive AHW. A small portion of the trail near North Redoubt is within the bounds of Hudson Highlands State Park. NYNJTC's East Hudson Trails #101 provides a map of the area.

Information in this article was obtained from, Desmond Fish Library, Garrison Union Free School District, Hudson River Valley Institute, Journal of the American Revolution, National Center for the American Revolution, New York-New Jersey Trail Conference, New York State Archives, United States Library of Congress, and Valley Forge Historical Society.




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